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Have you kept a Google or Outlook email?
(beehaw.org)
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this post was submitted on 05 Sep 2023
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Privacy
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Honestly email is the last frontier in privacy I haven’t been able to reform in my life… can’t self host since it’s a lot of work and trouble. And you gotta trust that companies will do the right thing with your data
An important first step that you can do before any "real" selfhosting is to get your own domain that you control. That way you can more easily switch providers (or start selfhosting) later on without having to distribute the knowledge of your changed email address to all relevant contacts and services.
I'm still using Gmail (lazy and it works), but I've switched fully to using only email addresses on domains that I own.
It is only a lot of work to set it up. Once done, though - just keep renewing the domain and applying updates to the server. ~5 moneyunits/month for the server and ~10/year for the domain. Get in touch if you're genuinely interested - I can give you a hand.
Out of curiosity, I’ve heard that emails being undelivered is a huge problem with self hosting as well since it gets flagged as spam. Is this something you’ve frequently encountered?
Also I appreciate the offer for help and will definitely consider it!
I've only really had issues with outlook rejecting email when I had DKIM config messed up, but it's been fine the last few years. I've emailed friends, companies, their support endpoints - it's worked well. There are penalties for new domains and new IPs used within the domain, but they go away in a week or so.